WEBVTT

1
00:00:00.100 --> 00:00:13.880
[upbeat music] Hey friend, it's David Nebinsky, the community lead here at the Chief of Staff Network.

2
00:00:14.100 --> 00:00:24.350
We help chief of staff through the three Cs: cohorts, curriculum, and community, via Slack with over 900 people in it. Learn more about membership and our upcoming events and programs at chiefofstaff.network.

3
00:00:24.820 --> 00:00:35.660
There you can see our upcoming fundamentals course cohort that starts at the end of March, and also our three Chief of Staff Connect conferences, with the first one being in San Francisco on May 15th through the 17th.

4
00:00:36.080 --> 00:00:44.520
In this episode, you'll learn from Ally Sardenia, the chief of staff at Order. This is Ally's second chief of staff role. She previously was a chief of staff at Managed by Q.

5
00:00:44.940 --> 00:00:55.269
In this episode, you'll learn about going from EA to chief of staff, how she got her current role, how Order is leaning into storytelling, what Ally's role b- has been in that, and so much more.

6
00:00:55.740 --> 00:01:08.010
Excited for you to level up as a chief of staff. Here we go with Ally. Okay, Chief of Staff podcast. Let's do it. Two-time chief of staff right here, y'all. Um, feel like that's like a [laughs]

7
00:01:08.060 --> 00:01:19.260
Some kind of like sporting event. And now- I know. Like I need a medal or something. [laughs] Trophy case. Well, y- you think so? We're working on it. W- I think, yeah Yeah... we're, we're building. We're building. Okay.

8
00:01:19.270 --> 00:01:30.720
Okay. Not quite, but we're working on it. Yeah. It's definitely, I mean, super impressive in my mind. Thank you. Thank you. Um, and I guess like how... This is, as you said, this is the second one.

9
00:01:31.050 --> 00:01:46.230
Um, how would you say you like started to get into this chief of staff world? Yeah. So, um, I joined my first startup in 2015, so this is about 10 years ago now. Um, company was called Managed by Q.

10
00:01:46.560 --> 00:02:02.540
So we were a workplace management platform. Um, and at the time, I joined as EA to the CEO. So I have gone through kind of like the EA to chief of staff, uh, kind of journey throughout my career, so not super novel.

11
00:02:02.600 --> 00:02:16.020
We can certainly talk about it. Um, but essentially, I think I was blessed to work with a bunch of leaders who were really like invested in me and my career and my passions and what I wanted to pursue.

12
00:02:16.740 --> 00:02:25.080
And so I think at some point, you know, while working, um, with our CEO and some of our other leaders, you know, it got to a point where they're like, "What are you, w- what are you interested in? What do you wanna do?"

13
00:02:25.640 --> 00:02:38.410
Um, because, and we can dig into this, you know, I was dealing with a lot of different things- Mm-hmm... outside the scope of just the EA role. Um, so obviously, my main thing was like CEO's life, his schedule- Mm...

14
00:02:38.410 --> 00:02:44.630
briefings, all of that. But when I joined, we had just raised our series A, and, uh, we had probably like 50 employees.

15
00:02:45.000 --> 00:02:57.880
So I was also tasked with things like employee engagement, so I was onboarding all of our new hires in a time when we were experiencing rapid growth, overseeing like program management, so all hands, like, you know, a, a lot of different things.

16
00:02:58.400 --> 00:03:07.930
So I think it just got to a point where, you know, people were like, "What is it that you wanna do?" [laughs] "You could go three different paths, honestly. Um, you could be a kind of like a career EA." Mm-hmm.

17
00:03:07.930 --> 00:03:11.240
"You can go that route, and we will keep building your skills in that direction."

18
00:03:11.940 --> 00:03:19.280
Uh, I was also overseeing our office, uh, so they were like, "You could be an office manager for your career, and you can do office build-outs and things like that."

19
00:03:19.320 --> 00:03:26.980
And then one day, I believe it was our head of people who was like, "Have you ever like heard of a chief of staff?" [laughs] She's like, "I think [laughs] you would be really good at it."

20
00:03:27.000 --> 00:03:33.860
And like, I was like, "I don't..." In my mind, I immediately was like, okay, government chief of staff is what you think about. Oh. And so I was like, I have...

21
00:03:33.900 --> 00:03:38.420
At the time, I think it was, the role was just kind of coming up, uh, so I didn't know too much about it.

22
00:03:38.740 --> 00:03:47.560
Started learning more about it, talking to her, talking to others, and that then just kind of became like my North Star for like where I knew I wanted to go in my career journey. Okay.

23
00:03:48.040 --> 00:04:00.070
And then like how you got that EA role, that was just like an- Yeah... applied online? Uh, uh, yeah. Actually, so, um, I moved to the city right after I graduated college, no job. I was like, "But I wanna be in the city.

24
00:04:00.120 --> 00:04:10.230
I'm gonna figure it out." I ended up, uh, through like my alma mater getting a job in PR. Mm-hmm. So I was in PR at first for like a year, realized just like wasn't for me. Mm-hmm.

25
00:04:10.240 --> 00:04:22.730
It's not the industry that I wanted to be in. Um, so I had reached out to a recruiter. Um, they had been amazing on my, you know, move to the city, helping me out, uh, all female-run recruiting firm, which was amazing.

26
00:04:22.900 --> 00:04:30.680
And they were like, "Hey, we're actually... Typically, we work with like hedge funds and things like that, which we know probably isn't for you.

27
00:04:30.740 --> 00:04:39.900
You seem more creative, like that doesn't seem like something would be motivating to you. But we got this role that came across our desk to be the EA for a CEO who works for this very mission-driven tech company."

28
00:04:40.020 --> 00:04:50.160
Mm-hmm. "And we think that you would be perfect for it." And so that's ultimately how- Okay... I ended up getting the EA role and kind of in the door of the startup. Okay. And then Managed by Q. Mm-hmm.

29
00:04:50.620 --> 00:05:02.140
Um, the company got acquired. Correct. And then, um, and you were the chief of staff then around then. Yep. And then, um, now you're chief of staff at Order.co. Correct, yep.

30
00:05:02.260 --> 00:05:14.040
Um, what was that kind of like transitional period or, or how did you then become the chief of staff at Order? Yeah. Um, so I would say, well, being at Managed by Q was probably...

31
00:05:14.160 --> 00:05:20.330
I was there for about four years going on five years. I would say like half of that time I was in the EA role. Mm-hmm.

32
00:05:20.330 --> 00:05:25.120
And a lot of that time was like spent in training and having conversations about here is what it takes to get to the next level.

33
00:05:25.560 --> 00:05:32.900
There actually was a little bit of a stepping stone where I, my role was manager of executive operations, and then eventually- Oh... turned to chief of staff- Okay...

34
00:05:32.920 --> 00:05:40.010
which was interesting, but like I was essentially kind of doing the work, but like I think candidly, I had a lot to learn. I was junior- Mm...

35
00:05:40.040 --> 00:05:48.520
and I was doing things for the first time, and there needed to be a good amount of training. So EA to manager of executive operations to then eventually chief of staff.

36
00:05:49.000 --> 00:05:56.120
Um, exactly like you said, we were acquired by WeWork, spun out, company was sold to a competitor. Mm.

37
00:05:56.130 --> 00:06:08.270
Um, so basically Managed by Q was kind of like disbanded, and after that, uh, it's funny enough, I found Order.co because my CEO at the time at Managed by Q was good friends with the CEO at Order.co- Mm...

38
00:06:08.270 --> 00:06:16.520
and was like, "Hey, just so you know, the company's about to be sold. She's about to be on the market. You should talk to her as soon as you can because I know that you're looking to hire a chief of staff."

39
00:06:16.640 --> 00:06:31.738
And that is how I got introduced to Zach, who is our CEO here at Order.co. Wow. Yeah. Okay. Yeah. It's been a journey. [laughs] Um-And, and so, like, Order. co at that time was, like, growing, et cetera. Mm-hmm.

40
00:06:31.748 --> 00:06:40.498
And then, like- Yeah... the CEO then was like, "Hey, I need someone to kinda- Yeah... to amplify me, take, take the company- Yeah... to the next level. I need a chief of staff," kind of thing? Yeah.

41
00:06:40.508 --> 00:06:49.098
Or- Yeah, so this was actually... This is a cool story. So it's funny also, I'm like tr- you know, realizing, like, I think I have maybe, like, a bread and butter spot here. Mm.

42
00:06:49.098 --> 00:06:57.738
Because when I joined, again, as mentioned, ManageByQ, so we had just raised our series A, we were probably by 50 employees, and that is exactly when I joined Order. Mm.

43
00:06:57.968 --> 00:07:07.188
Um, so I met with, um, our CEO, and he was just trying, you know, to talk to me about, "Hey, thinking about hiring a chief of staff."

44
00:07:07.428 --> 00:07:17.768
Um, and I basically told him, I was like, "Let's talk through the needs of your business, and then I will tell you what I think I am uniquely good at, and then we can decide together, is this the right fit or not?"

45
00:07:18.318 --> 00:07:28.568
I think, like, um, probably obvious, certainly to you, to others who may be listening, but, like, I believe that the chief of staff role is s- so tailored to the needs of the business- Mm...

46
00:07:28.608 --> 00:07:36.008
that we essentially sat down and crafted my role together. Um, so that was, like, a really good experience where he was like, um...

47
00:07:36.068 --> 00:07:41.158
Like, for example, at the time, they didn't really have anyone overseeing their people function. Mm.

48
00:07:41.188 --> 00:07:49.468
They had someone who had been there for a while who was quite junior who was doing an amazing job, but really needed someone to come in and kind of overhaul that for them. Same thing with kind of OKRs.

49
00:07:49.488 --> 00:07:56.198
They're like, "We're using OKRs, we're using goal setting, but, like, we're not doing it well. We need someone to come in and kind of like rehaul this for us."

50
00:07:56.228 --> 00:08:02.668
Really just, like, operational rigor and excellence, all those things, as they were thinking about growing the team.

51
00:08:02.788 --> 00:08:08.888
Um, so we had a really good conversation around like, okay, these are things that I have done before, I feel like I'm uniquely good at, can partner together.

52
00:08:09.008 --> 00:08:20.578
So again, we kind of crafted ourselves, which I thought was, like, an amazing way to go about it. Yeah. For sure. For sure. Like, hmm, seems like, uh... I mean, it's just win-win all around, right? Yeah.

53
00:08:20.608 --> 00:08:27.798
Like, you're kinda like, "Hey, I wanna make sure- Yeah... that, like, this is a good fit." Mm-hmm. Um, and I just love hearing that, like, they were pretty... They were open to it too. For sure.

54
00:08:27.828 --> 00:08:35.648
Like, versus, like- Yeah... "All right, 20 minutes with us. We know we're hiring someone." Yeah. Like- Yeah... "We're talking to a bunch of different people. Who's the best here?" Yeah. It was- Yeah.

55
00:08:35.688 --> 00:08:44.668
I think also, um, it was a good opportunity for me, too, to kind of, like, level set in terms of also what I wanted, or again, what I thought that I was good at.

56
00:08:45.208 --> 00:08:56.508
So I was like, "If you are looking for someone to essentially be your EA also on- Yeah... top of this," I was like, "That's not sustainable." Yeah. Um, I, I'm, I... That's not something that I'm interested in. Yeah.

57
00:08:56.577 --> 00:09:02.228
Um, so he was like, "Nope," like, I'm scheduling my own meetings. Five years later, he's still scheduling his own meetings. [laughs] I'm like, "So we gotta fix that."

58
00:09:02.438 --> 00:09:10.948
[laughs] But I'm like, "Hey, look, I set those boundaries from the beginning." Yeah. "And, like, we have abided by them, which is amazing." Um, was also like, "What does your finance team look like?

59
00:09:10.988 --> 00:09:20.297
Because I also am not, like, financially savvy in terms of- Mm... like I can't put together your strategic planning process, like build your operating plans. Like, that's just not my thing.

60
00:09:20.608 --> 00:09:25.468
If you need someone to project manage that- Yeah... and oversee that process, I can... Like, I'm your girl."

61
00:09:26.028 --> 00:09:31.038
And so again, I think that was a good opportunity to be like, I want to make sure that we are both set up for success here- Yeah...

62
00:09:31.068 --> 00:09:41.028
and that I'm being, you know, forthcoming around, like, what I think I am good at, and making sure that that, again, fits the needs of your business. And your sweet spot, sounds like you're saying, is like series A.

63
00:09:42.148 --> 00:09:54.267
Yeah, that was like, that like looking back, I, I don't know. Like, I think, like, that is a fun time, you know? [laughs] Like, it's a really fun time. It's chaos. [laughs] And I think that I'm really good at like,

64
00:09:55.388 --> 00:10:06.068
you know, like organizing folks through- Yeah... chaos, you know? Oh, yeah. Um, and I also feel like at that time, when the company's so small, like, you really feel like you are making an impact.

65
00:10:06.448 --> 00:10:14.788
Not that I don't feel that way today- Mm... but we have grown. We're a bigger company. I'm focused on different problems, which again, like, isn't a bad thing. These are good, like, new challenges.

66
00:10:14.808 --> 00:10:25.048
But I just think at the time, it's like you can kind of like go in, like figure out quickly, like, are, what needs to change, um, and you can kind of like feel that impact overnight, so to say. Yeah. Cool. Yeah.

67
00:10:25.108 --> 00:10:35.758
Um- It's interesting. So we kinda talked about your chief of staff- Mm-hmm... journey. Mm-hmm. Story. Story. Ooh. Oh, I see what you're doing. [laughs] Ooh. I see what you're doing.

68
00:10:35.797 --> 00:10:48.458
And I know you wanted to talk about storytelling. Storytelling, yep. Yeah. Mm-hmm. Um, I hear that storytelling is becoming, you know, um, a part of your role or something- Yeah... that you're thinking about these days.

69
00:10:48.937 --> 00:10:56.218
Yeah. Mm-hmm. What does that even look like? Yeah. Like, are you, are you saying, "Hey, I'm not going to work today. I'm going to The Moth- [laughs]... to just, like, chill and, like, learn about storytelling," or what?

70
00:10:56.248 --> 00:10:57.128
What's going down? Oh my God.

71
00:10:57.158 --> 00:11:10.488
It's so funny that you mention The Moth because this really all started with, um, my CEO and I last month read this book called Stories Sell by Matthew Dicks, and he is a prominent figure within The Moth.

72
00:11:10.988 --> 00:11:18.838
For those who aren't familiar, have... Are you familiar- Mm... with The Moth? I'm assuming so. Oh, yeah. Yeah. Well, I, I like... That, that was a throwaway joke, but I forgot- It-... that that was, uh- Okay.

73
00:11:18.838 --> 00:11:27.568
You, well, you nailed it. [laughs] You nailed the joke. Um, yeah, so The Moth is like a storytelling group. Yeah. Um, they have a podcast. Oh. So I would highly recommend listening to that.

74
00:11:27.748 --> 00:11:33.268
Um, they have in-person groups as well. But, like, they really have, like, perfected the craft- Mm... of storytelling.

75
00:11:33.348 --> 00:11:40.908
So we read this book because the, the context of the book is how to use stories to really, like, sell your brand and build kind of a brand strategy.

76
00:11:40.928 --> 00:11:58.098
And we were like, "This makes so much sense for our business," and, like, not to get too into the details, but, like, I think at a high level, we have a complex business, and we solve a lot of different problems for different constituents that oftentimes when talking to the market or talking to just really anyone- Yeah...

77
00:11:58.108 --> 00:12:03.908
if I'm talking to my family, like we joke internally, like, "Your mom does, has no idea what the company does." [laughs] Like, "What does the company do?"

78
00:12:04.028 --> 00:12:13.388
We are really like storytelling and telling who we are through a story really makes a lot of sense for us. Um, so

79
00:12:14.348 --> 00:12:25.628
after reading the story and talking to our, my, you know, my CEO, we are really like, this year's theme for us is storytelling, and we wanna think about how we can apply that through, like, various lenses of the business.

80
00:12:26.028 --> 00:12:33.108
So for example, there's things like all hands. Mm. Um, how can we embed stories into our presentations?

81
00:12:33.228 --> 00:12:44.738
So example, like a month ago, we had all of our, um, employees fly in for kind of like this annual kickoff, and we really spent a lot of time, like, leaning into stories, like customer stories.

82
00:12:44.768 --> 00:12:55.288
Like, don't just say, like, "Hey, you know, we helped this business save this much money," or, no, it's like, tell the story of like- Mm... who are these people and, like, what real problem did we solve for them?

83
00:12:55.348 --> 00:13:05.464
So it's like, you know-Emma at a cycling company Yeah Like we could just say like, "We saved her business," you know, however much money, and we consolidated however many like invoices.

84
00:13:05.484 --> 00:13:19.114
But no, like what really matters here is, you know, Zach walks into Emma's, you know, cycling studio and she says, "I came to this company because I really care deeply about the mission of this company- Mm-hmm...

85
00:13:19.194 --> 00:13:29.283
and like empowering other people, and I wanted to be a trainer and I wanted to build community, but now I'm chasing invoices, and like people are literally yelling at me 'cause I'm ordering the wrong like scrunchies."

86
00:13:29.624 --> 00:13:39.584
It's like the business, like what we are doing really matters- Yeah... and you don't really realize that until you like take a step back and like understand how we are helping like real people with real problems.

87
00:13:40.284 --> 00:13:50.744
Um, so we have tried to layer that into things like all-hands. Obviously from like a marketing and sales perspective, there's ways that you can lean into stories of how we have helped previous customers.

88
00:13:51.384 --> 00:13:57.004
A lot of it is also this concept of, um... I think my CEO's on like a rally cry right now of- Mm... show, don't tell.

89
00:13:57.624 --> 00:14:06.714
So even in the sales process it's like stop explaining to people what our business is and like what we can do, and show them. Demo them as soon as like humanly possible. Mm.

90
00:14:06.724 --> 00:14:12.974
Because people in their minds are trying to conceptualize what is it that you do. But once you see it, they're like, "Oh, okay, I got it. I got it."

91
00:14:13.584 --> 00:14:19.144
Um, and then the last piece I'll say is like that we're thinking about this year is potentially testing the market for a fundraise. Mm.

92
00:14:19.224 --> 00:14:34.384
And I think if we can really nail our story and we can, you know, be really thoughtful about how do we portray ourselves to investors in that sense, um, it will just, you know, it, it makes like a really big difference in terms of people understanding what it is we do today and what does that mean for us tomorrow.

93
00:14:35.724 --> 00:14:48.344
And what would you say is like your role in this part? Like- Yeah. So honestly, it's like furthering this in any capacity that I possibly can. So I think specifically for me, I would say all-hands is a big one.

94
00:14:48.464 --> 00:15:01.024
I oversee our all-hands. Um, so when we did that kickoff, I was working with my CEO to draft his speech. So a lot of my role also was like internal and ex- uh, mostly internal comms and like executive comms.

95
00:15:01.384 --> 00:15:07.604
So anything really our CEO is presenting, um, I'm helping him with the narrative there and the messaging there.

96
00:15:07.724 --> 00:15:14.864
So big part of that was partnering with him on like here is my keynote address to our employees and here's how we are going to embed stories into that.

97
00:15:14.924 --> 00:15:25.844
I also gave a presentation there in which I used a story myself- Oh... which was fun. Um, very different departure, like a very minimal slides. Like we can talk about that also- Yeah... because- Yeah...

98
00:15:25.914 --> 00:15:34.184
in the book there's like smaller tips for how to make presentations more engaging, and I think in startups, as chief of staff, we're probably working on presentations a lot.

99
00:15:34.284 --> 00:15:43.644
Um, so I just took a lot of that learning and, and, and really kind of like focused on making this, this kickoff focused on some of these learnings. Um, so it's things like that.

100
00:15:43.684 --> 00:15:53.204
We have bi- I- all-hands now happens bi-weekly, so every other week I'm now thinking like, "How can we fold in stories? How can we make this- Mm... more engaging for folks?" Um, can we try do something different?

101
00:15:53.744 --> 00:16:04.284
Um, and then outside of that I'm, again, as we think about potentially fundraising this year, spending a lot of time, um, with my CEO and thinking about what is our story, how do we craft that, and how do we, how do we share it.

102
00:16:05.784 --> 00:16:11.994
And so tell us, tell me about the like the story that you shared- Yeah... and like what- Yeah. Yeah, yeah. So I mean, I can walk through... Do you want me to like walk through the story?

103
00:16:12.064 --> 00:16:17.084
[laughs] Like essentially, so here- Sh- show, don't tell, yeah. [laughs] Yeah. Do you want me to sh- okay. I mean, I can. It's not, it's not a long story.

104
00:16:17.144 --> 00:16:30.484
So maybe the, the background context here is, um, I, outside of this, have another initiative for this year that folks are probably super familiar with, which is, um, you know, increasing context and exposure for leaders of the company really outside of our executive team.

105
00:16:30.964 --> 00:16:40.024
So as our company is growing, we wanna make sure that our full leadership has a, you know, understanding of how is the business performing, how is my work interacting with others, all of that.

106
00:16:40.704 --> 00:16:50.224
So really the whole point here is like I wanna get the right people in the right room- Mm... for the right conversations. Like that is like a, a really big other theme for me this year.

107
00:16:50.304 --> 00:17:01.344
So I basically share the story of, you know, it's 2015. Again, I'm working at my first startup, um, and I find myself in this leadership situation we can call it.

108
00:17:01.924 --> 00:17:13.704
Um, and it starts with a broken coffee machine, and David, on this morning something was brewing. Okay. It was not the coffee. Okay. I'm gonna tell you it's not the coffee. Um, I walk in and it is like

109
00:17:14.744 --> 00:17:25.424
there's extras from like The Last of Us walking around. People, empty coffee mugs, like nothing going on behind the eyes. We have dashboards, like TVs up on the walls of just like plummeting productivity.

110
00:17:25.704 --> 00:17:35.644
And I'm like something needs to happen fast because as a venture-backed startup, we're gonna run out of cash by like lunch if we don't get this turned around. So what do I do as, you know, a chief of staff?

111
00:17:35.764 --> 00:17:41.964
Someone like me, someone like everyone listening, jump into action, obviously. We need to solve this problem. So critical.

112
00:17:42.784 --> 00:17:49.583
I pull together a calendar invite and I remember throwing on a bunch of people that I'm like, "You know what? They're gonna help me fix this problem." Mm. We have to turn this around.

113
00:17:49.624 --> 00:17:59.244
We gotta get employee prod-productivity back up. Throwing on, uh, everyone that I can really think of to help solve this problem. Uh, the meeting invite just said like, "Help," H-A-L-P.

114
00:17:59.734 --> 00:18:10.824
[laughs] And the agenda was like the Java isn't javaing. So [laughs] people are like, "What is, what is going on?" Uh, we get in a room. I remember we have our IT manager there.

115
00:18:11.304 --> 00:18:15.304
He is just like frantically googling software updates for coffee machines.

116
00:18:16.044 --> 00:18:27.074
We have our head of HR who decides to use that as an opportunity to like propose this company-wide mindfulness program to wean everyone off of c- like caffeine entirely.

117
00:18:27.104 --> 00:18:33.724
Like it's chaos, and we're not getting any faster to the, to the solution here. At some point, um, there's a wrap on the door.

118
00:18:33.784 --> 00:18:40.974
Our office manager walks in and was like, "Hey, I'm catching wind of like what's going on here in this meeting. We have a repair guy like on speed dial for this.

119
00:18:41.384 --> 00:18:52.968
Slacked you his number, just give him a call and we'll get it fixed right away." Do you hear that silence?Everyone just stops and stares at me. [laughs] And they're like, "What? What are we doing here?"

120
00:18:53.028 --> 00:18:59.868
Like, slowly shaking their heads. S- uh, slow motion, everything's slow motion. Slowly closing their laptops. Slowly walking out the door.

121
00:19:00.248 --> 00:19:07.788
I call the repair guy, he's there w- within an hour, and the, like, the coffee machine is fixed. Productivity immediately increases. Phones are ringing off the hook with new business.

122
00:19:07.868 --> 00:19:14.308
No idea how it's related, but, like, it's happening. It's happening. Um, and we get acquired by lu- like, by dinner time.

123
00:19:14.768 --> 00:19:30.768
So the moral of the story here, that I share with everyone, is, like, this may seem like this was, like, a silly, silly blip in, like, a silly mistake that I made, but what it taught me is that it doesn't matter if you have the smartest people in the room.

124
00:19:30.828 --> 00:19:38.438
It doesn't matter if you have everyone in the room just because they have the same title. And I've made that mistake before, and I'm sure other people have made that mistake as well. Yeah.

125
00:19:38.438 --> 00:19:47.668
It is being incredibly, incredibly thoughtful about who is the right person or the right people to be solving this particular problem.

126
00:19:47.768 --> 00:19:55.988
Um, and that is kind of, like, how I had relayed to folks about how I am thinking about this year, um, and just being really, really thoughtful.

127
00:19:56.088 --> 00:20:07.188
Like, what are the key initiatives that our company has, and how do we maximize or, you know, increase our probability of success here by making sure that we have the right people around the table?

128
00:20:07.208 --> 00:20:11.988
And honestly, like, that means that we probably have folks in... outside of the executive team solving these problems.

129
00:20:12.048 --> 00:20:18.998
Like, we're, we're tapping in other leaders from the company, other ICs in the company because we believe that they are uniquely positioned to solve this problem.

130
00:20:19.518 --> 00:20:26.938
So that is kind of, like, one example of which, like, again, like, a silly thing, and this is, like, the first time that we are going through this.

131
00:20:26.948 --> 00:20:37.368
And, like, we're gonna learn how to tell stories really well, but this is just, like, an example of, like, people afterwards were like, "I wouldn't have remembered if you walked me through your strategy-" [laughs] "...

132
00:20:37.378 --> 00:20:39.868
of, like, here's exactly the people I'm gonna get in the room." Yeah. Like, no.

133
00:20:39.968 --> 00:20:50.628
Like, I actually remember that you told this, like, goofy story, and now I understand, like, what you're trying to do, and that's really all, like, that matters. And, hmm.

134
00:20:51.828 --> 00:21:00.527
And this, the all-hands, is that in person or virtual? In per- this one was in person. Okay, okay. So usually they are virtual. This one was, we flew all of our, um- Yeah... all of our staff in. All of the staff. Yeah.

135
00:21:00.588 --> 00:21:09.828
So it was good to have everyone there in person. Okay. Yeah. Um, and then when you think about these different com- like- Mm-hmm... when you were crafting the story, like, how were you thinking about the components?

136
00:21:09.888 --> 00:21:22.508
Yeah. Um, or are there components? Yeah. Or, like, what do you, like... So every time that you craft a story, like, the first thing that you wanna do is figure out, like, what is your realization? Mm.

137
00:21:22.868 --> 00:21:32.748
So you have to start, like, think about, like, I don't know, like a rom-com. Like, we, we give this example a lot too. It's like you're starting off somewhere, but you know, like, that's not...

138
00:21:32.788 --> 00:21:39.208
We're gonna have this character change. Like, this character's gonna go through it, and they're gonna come out a very different person.

139
00:21:39.248 --> 00:21:44.178
So you start somewhere, you end somewhere completely different, and you have this moment of realization. Mm-hmm.

140
00:21:44.528 --> 00:22:00.608
So I think, like, especially when we, um, not only kind of like that story that I shared, but, you know, for our CEO as well, we start with, like, what is the realization that this character or you have, and then kind of build the story around that realization as, like, the pivotal, the pivotal moment.

141
00:22:01.248 --> 00:22:13.888
Okay. Um, is there anything else about, like, crafting those stories? While, while you're thinking about that, I'm also curious about, like, like, what's really interesting about this is, like,

142
00:22:15.628 --> 00:22:28.328
like, this is initiative that doesn't have, like, clear ROI. Um, I mean, like- Yeah... we can point to the benefits of it, and we think that it- Mm-hmm...

143
00:22:28.348 --> 00:22:36.998
like, can lead to this, but I'm just, like, I guess more high level, I'm curious as to, like- Yeah... how you were able to, like, like, push this initiative forward- Yeah...

144
00:22:36.998 --> 00:22:45.348
when it's like, "Hey, this is a good idea," but there's- Yeah... like, the numbers are not, like, exactly tied to it. Mm-hmm. Mm-hmm. Yeah, so I think for us, like,

145
00:22:46.468 --> 00:22:56.138
when I think of ROI or, like, success of this initiative, all hands is certainly one of them, and I think there is a world in which... So we run engagement surveys, and we specifically- Mm...

146
00:22:56.208 --> 00:23:02.648
ask about all hands, and we gather data around, like, uh, the effectiveness of all hands. There's comments, open comments.

147
00:23:02.698 --> 00:23:10.028
Like, I'm looking there to understand, like, are people engaging with the content here, and are they understanding it more? And it's, like, that's one place to look at it.

148
00:23:10.048 --> 00:23:19.108
From a fundraising perspective, like, there could definitely be- [laughs]... an ROI there, for sure. [laughs] Um, and that's gonna be a quick way to figure out, like, is this working or not working?

149
00:23:19.148 --> 00:23:27.608
And honestly, one of the big reasons of why we are focusing on that this year is, like, it has not... Like, we haven't perfected our story before. Mm.

150
00:23:27.648 --> 00:23:34.928
And we've gotten that feedback, like, especially externally, where it's like, "We need a really clear understanding of what it is that you do." Ah.

151
00:23:34.938 --> 00:23:38.938
And so a lot of, like, why we have launched this initiative is because of that feedback.

152
00:23:39.268 --> 00:23:47.508
So I do think that, like, fundraising this year will be a really good indicator of, is this initiative actually moving the needle in the way that we want it to?

153
00:23:47.628 --> 00:23:57.558
Um, I mentioned, like, kind of like marketing and sales, and, like, this is something that I'm not necessarily overseeing. Um, but there's obviously, like, a really clear opportunity to measure, you know- Yeah...

154
00:23:57.568 --> 00:24:07.908
close rate, things like that. Yeah. And seeing if, like, your shifting your narrative or your stories impacts your ability to close a deal or not, that's one way in which the team can, can assess that, for sure. Yeah.

155
00:24:07.918 --> 00:24:15.658
Yeah, and I guess, like, within the all hands is, like, if people aren't engaging, then maybe they're, like, not having a good time with the company. Sure. And if they're not having a good time with the company- Yeah...

156
00:24:15.668 --> 00:24:20.098
maybe they leave. Yeah. And then if they leave, then it's like- Yeah. Yeah... um.

157
00:24:20.188 --> 00:24:29.248
I actually think that, like, I was on your website a little bit earlier today, and I really liked the, like, at the top where it says, like, "Why Order?" Mm-hmm. And it's just like boom, boom, boom. Yes, yes. Yeah.

158
00:24:29.348 --> 00:24:38.708
Um, and yeah, kinda, like, jealous of that. [laughs] I mean, yeah. I mean, that's all props to our marketing team. [laughs] Like, they're doing an amazing job.

159
00:24:39.208 --> 00:24:47.108
Again, like, they're, they're figuring out a way of, like, how do we explain what our business does and the problems that we solve in, like, a succinct way. Yeah.

160
00:24:47.158 --> 00:24:53.318
Yeah, we launched that, like, Why Order page, I would say, mm, it's maybe, like, two years ago now. Okay. And it's been, like, massively helpful. Got it.

161
00:24:53.328 --> 00:25:05.833
So things like that, I think our marketing team, like, is crushing, so yeah, huge props to our team on that. Cool. Yeah. Um-How else is like storytelling like flowing through in the company and your role? Yeah Yeah.

162
00:25:05.884 --> 00:25:15.544
So, um, the other thing that I think was helpful, um, in the book that we read was like, again, little tips for like presentations that- Mm...

163
00:25:15.554 --> 00:25:26.784
I have also taken away as someone, again, who builds a lot of decks and like sees a lot of decks. Um, there was just like maybe like two or three tips that like really stood out to me.

164
00:25:26.844 --> 00:25:34.974
So one was, I think a lot of people get in the habit of like the minute that they need to create a presentation, they go right into PowerPoint or, or Google Doctor- Mm. Yeah...

165
00:25:34.984 --> 00:25:43.024
like whatever, and they, uh, start building the slides, and then they try and figure out, okay, what's my talk track like around this? Or like- Yeah... what's my talk track for each slide?

166
00:25:44.184 --> 00:25:51.784
The thing that like I have been doing for quite some time now, but like was reinforced, was like start with the story or start- Mm... with the narrative.

167
00:25:52.224 --> 00:26:05.564
So actually like write it out first, and then once you have really nailed that narrative, go in and see like what are the inflection points or what are the areas of the narrative that can be reinforced by visuals.

168
00:26:05.704 --> 00:26:20.384
Um, so if your presentation then is three slides, but the visuals are super impactful to supporting your narrative, like that's amazing, versus kind of like flipping through hundreds of slides, a lot of text on slides.

169
00:26:20.504 --> 00:26:30.944
I think then people start to kind of like lose their engagement a little bit. That's one way to do it. Um, there were also like some really silly ones, honestly- [laughs]... that I'm like, I never...

170
00:26:31.424 --> 00:26:42.714
I like see what you're saying now, but like I never really thought of it. Like build, like use builds. So like if you have a list of stuff, use builds because you are literally building suspense.

171
00:26:42.804 --> 00:26:50.674
[laughs] And I was like, I never- Use builds? As in like- Like use, like so if you have like a, like one, you show one, uh, bullet- Yeah...

172
00:26:50.704 --> 00:26:59.164
your point, don't show anything else, and then you have to click again to show the second bullet point. Ah. The third bullet point. So like really like a click-through, like a build for your points. Got it.

173
00:26:59.204 --> 00:27:10.444
Otherwise, like what tends to happen is people zone out on what you're saying. They're just reading the slide. They're like kind of onto the next thing. But this keeps people engaged with your content and your material.

174
00:27:10.464 --> 00:27:17.944
And again, like people then are like, "Okay, I'm seeing a list here. Now you've gone through the first thing." Yeah. "I really wanna know what's your second, like what's your second point?" Yeah.

175
00:27:17.984 --> 00:27:28.164
It's like a really, again, it's a really minor thing, but tips like that I've now been, has been in the back of my mind, and I've been incorporating it in every, you know, presentation that I've pulled together since.

176
00:27:28.704 --> 00:27:36.084
Um, so that's just another way that I'm trying to just like take some of these tips, um, and just try to make some of the content a little bit more engaging. Yeah.

177
00:27:37.844 --> 00:27:46.304
What else would you say is like you're really focused on these days, um... Yeah. Yeah. So the other thing, kind of like back to the story there, was kind of like, you know, woven in there.

178
00:27:46.324 --> 00:27:59.274
But again, it is really focused on increasing exposure and context for our leaders at the company. Um, as our company has grown, again, I joined, we were like 50 people. We're now like 120, I would say. Wow.

179
00:27:59.404 --> 00:28:13.544
Um, the team has grown a lot, and so like it's always this constant battle, like figuring out of like who needs to know what information when, who needs even what information, um, like who needs to know what before it's shared at an all hands.

180
00:28:13.604 --> 00:28:24.604
Like- Mm... it, it's just a lot of stuff to figure out. Last year or maybe the year before, like we went through, um, kind of a process where e- even now we have an exec team. The exec team is large, though.

181
00:28:24.684 --> 00:28:32.544
I'd say there's about like 10 people on our executive team. And so we're finding like that's actually no longer the best place to be like problem-solving. Mm.

182
00:28:32.624 --> 00:28:42.004
We have a lot of people in that room, and not everyone has, you know, the credibility or whatever to be solving a specific problem. Like our head of engineer doesn't need to be solving like a marketing...

183
00:28:42.144 --> 00:28:48.304
You know what I'm saying? Yeah, yeah, yeah. Like, and so we're trying to figure out like, okay, how do we go about doing that? And then also what I said, who are the right people?

184
00:28:48.674 --> 00:28:56.984
So if there are people who are not necessarily on the exec team that we believe are actually best suited to be the person like addressing this problem, like let's get them in.

185
00:28:57.664 --> 00:29:10.973
So, um, we've like really revamped our operating rhythm. Like we're not even- Mm... doing OKRs anymore. Mm. So what we are doing this year is, um, really everything is structured around key company initiatives.

186
00:29:11.364 --> 00:29:20.754
Now, each key company initiative has goals that, you know, we need to hit within each of those, but we're not necessarily doing like the OKR like kind of like dar- like by department- Yeah... type thing. Yeah.

187
00:29:20.804 --> 00:29:26.854
So it's like, okay, here's the key company initiatives. Here are the goals. Here is visibility into who is like sponsoring these.

188
00:29:26.884 --> 00:29:35.113
So we have sponsors that are on the exec team, but we also have sponsors who are not on the exec team, so like a really good opportunity for other- Mm... leaders to like step up and have ownership over these initiatives.

189
00:29:35.864 --> 00:29:45.363
And then have structured our exec team meetings and then also smaller group, like more tactical moving the initiative forward meetings that are happening on a biweekly basis.

190
00:29:45.464 --> 00:29:54.404
Um, so that has been like my big thing, like what is the right structure here? What is the right way to get people kind of like involved that should be involved, that weren't involved before?

191
00:29:54.444 --> 00:29:59.904
It's really just like a lot of rethinking, again, that kind of like operating rhythm and how we're, we're attacking problems.

192
00:29:59.964 --> 00:30:07.194
That's been another big focus for me this quarter and certainly will persist, I think, throughout the year. So you're revamping this, and I- Mm-hmm...

193
00:30:07.204 --> 00:30:18.844
can imagine then like in this process you're probably like kicking some people out or like- Yeah... are you using storytelling a part of that? [laughs] So that is like, I mean, that is a great question. Um, so like yeah.

194
00:30:18.884 --> 00:30:30.684
So right now in Q1, we're gonna have all of the same people like attacking these problems, but, you know, initiatives could change in, uh, Q2 as we learn, and things could, like people could be swapped out, and I've thought a lot about that.

195
00:30:30.704 --> 00:30:38.144
I'm like, oh- Mm... is that tough that like you have one person that has this context, and then next quarter, like maybe they don't have that visibility anymore? Mm.

196
00:30:38.284 --> 00:30:54.104
The best way that like I like can explain this or I've explained it to other people, and like actually it's funny because we're not using OKRs, but this like this idea has k- come to mind from me before where the idea of OKRs, but I'm using the, in the sense for like our initiatives, is like you think of a spotlight.

197
00:30:54.744 --> 00:31:05.682
So-We as a business need to spotlight the areas that we know, like, require attention or, like, we need to make progress on. But if we feel like we've, you know, made progress there- Yeah...

198
00:31:05.712 --> 00:31:15.612
or we need to shift strategy, the spotlight changes. And if the spotlight changes, it's natural that we're gonna need to think about then who are the right people then to go to this other spotlight?

199
00:31:15.652 --> 00:31:19.752
Who are the other people that need, should be involved in kind of these new initiatives?

200
00:31:19.772 --> 00:31:29.652
So the best way that I can think about it is, like, we spotlight certain initiatives, and if those, that spotlight changes, it's natural that we need to rethink, okay, who are the right people around the table in, in that sense.

201
00:31:29.872 --> 00:31:39.552
Yeah. I like that. It sounds like that's, like, more of, like, not necessarily, like, removing people. It's more about like- Right... who's a better fit for this current focus- Yeah... of... Yeah.

202
00:31:39.682 --> 00:31:40.702
And I think people get that. Yeah.

203
00:31:40.752 --> 00:31:49.132
Like, the sense that I've gotten from leaders is, like, we totally, we totally get that, and it's also, like, just because you're not involved this quarter doesn't mean you're not ever gonna be involved.

204
00:31:49.172 --> 00:31:54.272
[laughs] Like, you probably will have an opportunity- Yeah... in the next quarter, so, like, that should be, like, exciting to you. Yeah.

205
00:31:54.292 --> 00:32:02.172
And also, just because, like, y- you know, maybe an initiative isn't spotlighted that you're in, like, the work that you're still doing is very important. Like, there's a lot of work to be done.

206
00:32:02.182 --> 00:32:11.172
So I just kind of, like, people have, at least internally, like, really kind of, like, understood this, like, spotlight concept, and I think people kind of get what that means and what it means for them in particular.

207
00:32:11.612 --> 00:32:26.952
Nice. Yeah. Um, are there any, like, tools or hacks or anything like that that, like, you swear by that, like- Yeah. Yeah. Um, that's a good question. So it's funny because, like, we have previously...

208
00:32:27.012 --> 00:32:32.452
I think for, like, a lot of housing, some of this has been, like, within, um, Google Drive.

209
00:32:32.482 --> 00:32:38.502
And because, like, we're doing something sufficiently different, what we have now done is created one-pagers for each initiative- Mm...

210
00:32:38.572 --> 00:32:47.152
and that has been shared out to the entire company, and then we house that on kind of, like, a better branded, uh, like, you know, one-pager type thing.

211
00:32:47.232 --> 00:32:53.482
So it's like a repository or collection of all of these one-pagers that I've been able to brand. Like, it looks pretty nice. Mm.

212
00:32:53.482 --> 00:32:58.602
Um, so that has been, like, a really helpful way to be, like, there's a lot of information, there's a lot of stuff that we're working on.

213
00:32:58.652 --> 00:33:07.072
Here is a literal one-pager per initiative that tells you just, like, the high level that, like, you need to know. Yeah. So it's basically like, you know, what is the initiative? What are we trying to accomplish?

214
00:33:07.172 --> 00:33:15.072
How are we measuring success? Who are the sponsors of this? Mm. Um, and that's sh- these are all shared around with everyone in the company for their visibility.

215
00:33:15.082 --> 00:33:21.712
That is something new that we have tried this year, and I think it's gotten, um, pr- some pretty good feedback, honestly.

216
00:33:21.752 --> 00:33:32.282
What I've heard from folks is they're like, "Using kind of, like, this format and sharing it around in this way really gives me a much better sense of, like, what other people in the company are working on." Mm.

217
00:33:32.292 --> 00:33:36.972
And it actually then opens the door for more, like, cross-functional collaboration. Yeah.

218
00:33:37.032 --> 00:33:45.802
Because now I'm like, "I know that this is your priority, and I know that this isn't, so I'm not gonna bother you about this thing." [laughs] "But now I'm gonna talk to you about this thing." Yeah. Um, yeah.

219
00:33:45.832 --> 00:33:48.392
So, like, I think, like, again, it's what? Mid-February.

220
00:33:48.452 --> 00:33:58.292
Like, we're still kind of, like, really getting into the process here, but, like, so far I think folks are feeling good about, like, this iteration more so than they have previously.

221
00:33:58.412 --> 00:34:05.892
So it's definitely a departure, [laughs] but, like, it's working- Yeah... so I'm like, "Whatever. [laughs] We'll, we'll run with it." Nice. Nice. Yeah. Nice. Yeah.

222
00:34:07.152 --> 00:34:18.732
Yeah, I think, like, that idea of, like, how do you kind of, like, organically get cross- Yeah... cross-department collaboration- Yeah... um, versus, like, maybe, like, forcing it. Yeah. Yeah. Um. Yeah. That's nice.

223
00:34:18.932 --> 00:34:32.302
Yeah. I like that. Yeah. The, people appreciate the visibility. Yeah. People really appreciate the visibility. Yeah. So. Um, anything else you wanna share to existing chiefs of staff, aspiring chiefs of staff? Yeah.

224
00:34:32.332 --> 00:34:47.652
I mean, I think, like, especially aspiring chiefs of staff, well, one, I'm always happy to talk to folks who are interested in moving into the chief of staff, uh, role, especially for those who kind of had a similar career journey going from, like, EA to chief of staff.

225
00:34:47.792 --> 00:34:55.951
Um, yeah, like, I think, like, my advice there is, like, take on as many challenges- Mm... as you possibly can, even if it makes you uncomfortable.

226
00:34:56.132 --> 00:35:04.112
I think the opportunities and the times in which, like, I have personally grown and developed have been times that have just, like, candidly scared me shitless.

227
00:35:04.122 --> 00:35:10.392
[laughs] When I've been asked to do something that I have never done before, and just it was kind of like sink or swim, figure [laughs] figure it out. Yeah.

228
00:35:10.932 --> 00:35:18.032
Um, that was the best, like, possible learning opportunity for me. Um, it, I think, like, you know, a lot of people say this before, but, like,

229
00:35:19.032 --> 00:35:27.062
when you feel like you have nothing more to learn, that's when you know it kind of, it's like your time to, like, move forward. I can say, like, I'm still learning so much in this role. Mm.

230
00:35:27.072 --> 00:35:38.052
Having been through it two times now, probably going on, like, eight years, um, there's just a lot to learn still, and there's a lot of different challenges, which I think keeps the role fresh and exciting.

231
00:35:38.602 --> 00:35:48.392
So yeah, I think, like, keep learning, um, especially, again, if you're looking to go into the role. Like, challenge yourself quite a bit. Mm. And I'm always happy to help however I can. Happy to talk to people. Yeah.

232
00:35:48.572 --> 00:35:56.092
Reach out to you on LinkedIn with the best, the world's best LinkedIn banner. [laughs] That's right. That's right. The banner that's never gonna go away. [laughs] It's always gonna be there.

233
00:35:56.112 --> 00:36:04.502
[laughs] We were j- I'm not changing it... we were joking about it before we started this. [laughs] I was like, "I wonder where this banner came from." Yeah. It came from a company photo shoot that we had. I think...

234
00:36:04.992 --> 00:36:13.562
Oh, my God, my hair is so short in, shorter than that, and my hair's long now. Um, I think, like, 2016 it's from. Okay. But I'm never changing it- [laughs]...

235
00:36:13.592 --> 00:36:23.162
despite, like, our marketing team and all of our employees changing their banners to an Order.co banner. I'm like, "I can't do it, you guys. I just can't." [laughs] But they respect it. They respect it. Yeah. Yeah.

236
00:36:23.192 --> 00:36:27.972
I love it. Well, thank you so much, Ally. We really appreciate it. Thank you so much for having me. It's a pleasure. Whoop, whoop.

237
00:36:30.772 --> 00:36:50.252
[outro music]